This invention relates to processes for the preparation of [1-oxo-2-phenyl, halophenyl or thienyl-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid (I, below) and to the nontoxic pharmaceutically acceptable salt, ester and amides thereof: ##SPC1##
Wherein R.sup.2 is phenyl, halophenyl, particularly chlorophenyl or fluorophenyl, or thienyl, particularly the 2-thienyl.
This invention also relates to useful intermediates in the preparation of I having the structures: ##SPC2##
Wherein R.sup.2 is phenyl, halophenyl or thienyl and R is CH.sub.2 COOH, R.sup.1 or CH.sub.2 COOR.sup.1, and wherein R.sup.1 is lower alkyl or halo lower alkyl such as methyl, ethyl, isopropyl, trifluoromethyl, butyl, propyl and the like; aryl such as phenyl and nuclear substituted derivatives thereof such as nitrophenyl, tolyl, xylyl, ethylphenyl and the like; aralkyl and nuclear substituted aralkyl having from 7 to about 20 carbon atoms such as benzyl, p-chlorobenzyl, p-nitrobenzyl and the like; and wherein X is OH, halo, and acid ester moieties such as trifluoroacetate, tosylate, acetate and the like.
The indanones of structure I and the nontoxic pharmaceutically acceptable salt, ester and amide derivatives, have diuretic, saluretic and uricosuric activity.
Thus, it is an object of the present invention to provide a specific, unified process for the preparation of [1-oxo-2-phenyl, halophenyl or thienyl-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid and the nontoxic pharmaceutically acceptable salt, ester and amide derivatives thereof. It is also an object of the present invention to provide useful intermediates (III, IV, and V, above-described) which are involved in the process of this invention.